Organic Chemistry Portal

Abstracts

Search:

Syntheses of Unsymmetrical 1,4-Bifunctional Allylboron Reagents via Cu-catalyzed Highly Regio- and Stereoselective 1,4-Protoboration of Dienylboronates and Analysis of the Origin of Chemoselective Aldehyde syn-(Hydroxymethyl)allylation

Shang Gao, Mengzhou Wang, Ming Chen*

*Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849, United States, Email: mzc0102auburn.edu

S. Gao, M. Wang, M. Chen, Org. Lett., 2018, 20, 7921-7925.

DOI: 10.1021/acs.orglett.8b03483


Abstract

Cu-catalyzed highly regio- and stereoselective 1,4-protoboration of dienylboronates provides unsymmetrical 1,4-bifunctional allylboron reagents. A subsequent chemoselective allylboration with aldehydes followed by oxidative workup give diol products with high diastereoselectivity.

see article for more examples

see article for more examples



Development of α-Borylmethyl-(Z)-crotylboronate Reagent and Enantioselective Syntheses of (E)-δ-Hydroxymethyl-syn-homoallylic Alcohols via Highly Stereoselective Allylboration

J. Liu, S. Gao, M. Chen, Org. Lett., 2021, 23, 9451-9456.


Key Words

allylboronates, homoallylic alcohols, 1,3-diols, hydrogen peroxide


ID: J54-Y2018